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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/69/4126900.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4126900
loop_
_publ_author_name
'Wu, Yilei'
'Han, Ji-Min'
'Hong, Michael'
'Krzyaniak, Matthew D.'
'Blackburn, Anthea K.'
'Fernando, Isurika R.'
'Cao, Dennis D.'
'Wasielewski, Michael R.'
'Stoddart, J. Fraser'
_publ_section_title
;
 X-Shaped Oligomeric Pyromellitimide Polyradicals.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b12124
_journal_year                    2017
_chemical_formula_moiety         'C44 H22 N4 O8'
_chemical_formula_sum            'C44 H22 N4 O8'
_chemical_formula_weight         734.65
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.469(2)
_cell_length_b                   15.469(2)
_cell_length_c                   34.551(5)
_cell_measurement_reflns_used    1639
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      49.555
_cell_measurement_theta_min      4.785
_cell_volume                     8267.7(19)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.571
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1425
_diffrn_reflns_av_unetI/netI     0.1096
_diffrn_reflns_Laue_measured_fraction_full 0.571
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9253
_diffrn_reflns_point_group_measured_fraction_full 0.571
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         50.497
_diffrn_reflns_theta_min         4.785
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.7500
_exptl_absorpt_correction_T_min  0.3955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1357 before and 0.0712 after correction.
The Ratio of minimum to maximum transmission is 0.5273.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       prism
_exptl_crystal_F_000             3024
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1150P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.1911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1236
_reflns_number_total             2142
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12124_si_002.cif
_cod_data_source_block           i41-a
_cod_original_cell_volume        8268(3)
_cod_database_code               4126900
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.915
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
;
_smtbx_masks_special_details
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  Only the
atoms used in the refinement model are reported in the formula here.

Total solvent accessible volume / cell = 2094.1 Ang^3 [25.3%]
Total electron count / cell = 40.9
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.4686(2) 0.5798(3) 0.91103(10) 0.0613(11) Uani 1 1 d .
O2 O 0.3706(2) 0.3015(2) 0.89776(10) 0.0558(10) Uani 1 1 d .
O3 O 0.7112(2) 0.4698(3) 1.03512(10) 0.0618(11) Uani 1 1 d .
O4 O 0.6299(2) 0.1875(3) 1.01731(11) 0.0692(12) Uani 1 1 d .
N1 N 0.4048(3) 0.4478(3) 0.89647(12) 0.0512(12) Uani 1 1 d .
N2 N 0.6869(3) 0.3211(3) 1.03296(14) 0.0617(13) Uani 1 1 d .
C1 C 0.2406(5) 0.5302(4) 0.8081(2) 0.0744(19) Uani 1 1 d .
H1 H 0.2030 0.5492 0.7881 0.089 Uiso 1 1 calc R
C2 C 0.3258(5) 0.5529(4) 0.80660(17) 0.0717(18) Uani 1 1 d .
H2 H 0.3469 0.5878 0.7860 0.086 Uiso 1 1 calc R
C3 C 0.2083(4) 0.4819(4) 0.8368(2) 0.0686(17) Uani 1 1 d .
H3 H 0.1487 0.4668 0.8368 0.082 Uiso 1 1 calc R
C4 C 0.3822(4) 0.5239(4) 0.83592(18) 0.0651(16) Uani 1 1 d .
H4 H 0.4423 0.5367 0.8351 0.078 Uiso 1 1 calc R
C5 C 0.2617(4) 0.4533(4) 0.86712(18) 0.0662(17) Uani 1 1 d .
H5 H 0.2393 0.4195 0.8877 0.079 Uiso 1 1 calc R
C6 C 0.3474(4) 0.4762(3) 0.86589(17) 0.0551(15) Uani 1 1 d .
C7 C 0.4617(3) 0.5024(4) 0.91538(16) 0.0519(14) Uani 1 1 d .
C8 C 0.4138(3) 0.3620(4) 0.90863(15) 0.0504(14) Uani 1 1 d .
C9 C 0.5118(3) 0.4476(3) 0.94246(14) 0.0467(14) Uani 1 1 d .
C10 C 0.4834(3) 0.3635(3) 0.93904(14) 0.0468(14) Uani 1 1 d .
C11 C 0.5743(3) 0.4725(3) 0.96928(16) 0.0535(15) Uani 1 1 d .
H11 H 0.5912 0.5310 0.9728 0.064 Uiso 1 1 calc R
C12 C 0.5168(3) 0.2948(3) 0.96060(16) 0.0495(14) Uani 1 1 d .
C13 C 0.6097(3) 0.4049(3) 0.99042(14) 0.0495(14) Uani 1 1 d .
C14 C 0.5815(3) 0.3202(3) 0.98638(15) 0.0492(14) Uani 1 1 d .
C15 C 0.6740(4) 0.4084(4) 1.02211(16) 0.0544(15) Uani 1 1 d .
C16 C 0.6320(4) 0.2650(4) 1.01270(17) 0.0572(15) Uani 1 1 d .
C17 C 0.7437(4) 0.2918(4) 1.06278(19) 0.0644(16) Uani 1 1 d .
C18 C 0.8186(4) 0.2497(4) 1.0537(2) 0.0745(18) Uani 1 1 d .
H18 H 0.8357 0.2444 1.0274 0.089 Uiso 1 1 calc R
C19 C 0.7178(5) 0.3027(4) 1.1005(2) 0.083(2) Uani 1 1 d .
H19 H 0.6658 0.3325 1.1065 0.100 Uiso 1 1 calc R
C20 C 0.8696(4) 0.2146(4) 1.0826(3) 0.082(2) Uani 1 1 d .
H20 H 0.9216 0.1848 1.0765 0.099 Uiso 1 1 calc R
C21 C 0.7701(5) 0.2687(4) 1.1299(2) 0.090(2) Uani 1 1 d .
H21 H 0.7544 0.2769 1.1562 0.108 Uiso 1 1 calc R
C22 C 0.8429(5) 0.2242(4) 1.1209(2) 0.083(2) Uani 1 1 d .
H22 H 0.8763 0.1991 1.1411 0.099 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C7 N1 C6 123.4(4) .
C7 N1 C8 111.9(5) .
C8 N1 C6 124.6(4) .
C15 N2 C17 125.5(5) .
C16 N2 C15 111.9(5) .
C16 N2 C17 122.4(5) .
C2 C1 H1 119.0 .
C3 C1 H1 119.0 .
C3 C1 C2 122.1(6) .
C1 C2 H2 120.4 .
C1 C2 C4 119.3(6) .
C4 C2 H2 120.4 .
C1 C3 H3 119.7 .
C1 C3 C5 120.6(6) .
C5 C3 H3 119.7 .
C2 C4 H4 121.1 .
C6 C4 C2 117.9(6) .
C6 C4 H4 121.1 .
C3 C5 H5 121.2 .
C6 C5 C3 117.7(6) .
C6 C5 H5 121.2 .
C4 C6 N1 118.1(5) .
C5 C6 N1 119.4(5) .
C5 C6 C4 122.5(6) .
O1 C7 N1 126.9(5) .
O1 C7 C9 126.7(5) .
N1 C7 C9 106.4(5) .
O2 C8 N1 125.9(5) .
O2 C8 C10 128.6(5) .
N1 C8 C10 105.4(5) .
C10 C9 C7 108.6(5) .
C10 C9 C11 122.6(5) .
C11 C9 C7 128.7(5) .
C9 C10 C8 107.6(5) .
C9 C10 C12 123.7(5) .
C12 C10 C8 128.7(5) .
C9 C11 H11 122.7 .
C13 C11 C9 114.5(5) .
C13 C11 H11 122.7 .
C10 C12 C12 125.7(5) 6_554
C10 C12 C14 113.0(4) .
C14 C12 C12 121.0(5) 6_554
C11 C13 C15 128.8(5) .
C14 C13 C11 122.3(5) .
C14 C13 C15 108.7(5) .
C12 C14 C16 127.6(5) .
C13 C14 C12 123.7(5) .
C13 C14 C16 108.6(5) .
O3 C15 N2 126.1(5) .
O3 C15 C13 129.0(5) .
N2 C15 C13 104.8(5) .
O4 C16 N2 124.3(5) .
O4 C16 C14 130.0(5) .
N2 C16 C14 105.7(5) .
C18 C17 N2 120.4(6) .
C18 C17 C19 121.6(6) .
C19 C17 N2 117.8(6) .
C17 C18 H18 119.9 .
C17 C18 C20 120.3(7) .
C20 C18 H18 119.9 .
C17 C19 H19 120.9 .
C17 C19 C21 118.3(6) .
C21 C19 H19 120.9 .
C18 C20 H20 120.8 .
C18 C20 C22 118.3(6) .
C22 C20 H20 120.8 .
C19 C21 H21 119.8 .
C22 C21 C19 120.3(7) .
C22 C21 H21 119.8 .
C20 C22 H22 119.5 .
C21 C22 C20 121.1(6) .
C21 C22 H22 119.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.212(6) .
O2 C8 1.209(6) .
O3 C15 1.199(6) .
O4 C16 1.209(6) .
N1 C6 1.448(7) .
N1 C7 1.384(7) .
N1 C8 1.400(7) .
N2 C15 1.415(7) .
N2 C16 1.403(7) .
N2 C17 1.428(7) .
C1 H1 0.9500 .
C1 C2 1.366(9) .
C1 C3 1.340(9) .
C2 H2 0.9500 .
C2 C4 1.410(8) .
C3 H3 0.9500 .
C3 C5 1.404(8) .
C4 H4 0.9500 .
C4 C6 1.381(8) .
C5 H5 0.9500 .
C5 C6 1.374(8) .
C7 C9 1.481(7) .
C8 C10 1.505(7) .
C9 C10 1.378(7) .
C9 C11 1.393(7) .
C10 C12 1.397(7) .
C11 H11 0.9500 .
C11 C13 1.389(7) .
C12 C12 1.480(10) 6_554
C12 C14 1.397(7) .
C13 C14 1.387(7) .
C13 C15 1.480(7) .
C14 C16 1.472(7) .
C17 C18 1.366(8) .
C17 C19 1.374(9) .
C18 H18 0.9500 .
C18 C20 1.384(8) .
C19 H19 0.9500 .
C19 C21 1.399(9) .
C20 H20 0.9500 .
C20 C22 1.395(10) .
C21 H21 0.9500 .
C21 C22 1.357(9) .
C22 H22 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C7 C9 C10 178.9(5) . .
O1 C7 C9 C11 2.5(8) . .
O2 C8 C10 C9 -177.7(5) . .
O2 C8 C10 C12 2.9(8) . .
N1 C7 C9 C10 -0.3(5) . .
N1 C7 C9 C11 -176.7(5) . .
N1 C8 C10 C9 -1.1(5) . .
N1 C8 C10 C12 179.6(5) . .
N2 C17 C18 C20 -174.3(5) . .
N2 C17 C19 C21 175.6(5) . .
C1 C2 C4 C6 -2.5(8) . .
C1 C3 C5 C6 -0.5(8) . .
C2 C1 C3 C5 0.7(9) . .
C2 C4 C6 N1 -178.7(5) . .
C2 C4 C6 C5 2.8(8) . .
C3 C1 C2 C4 0.8(9) . .
C3 C5 C6 N1 -179.8(5) . .
C3 C5 C6 C4 -1.4(8) . .
C6 N1 C7 O1 4.4(8) . .
C6 N1 C7 C9 -176.4(4) . .
C6 N1 C8 O2 -6.4(8) . .
C6 N1 C8 C10 176.8(4) . .
C7 N1 C6 C4 49.5(7) . .
C7 N1 C6 C5 -132.0(5) . .
C7 N1 C8 O2 177.7(5) . .
C7 N1 C8 C10 0.9(5) . .
C7 C9 C10 C8 0.8(5) . .
C7 C9 C10 C12 -179.8(5) . .
C7 C9 C11 C13 -179.8(5) . .
C8 N1 C6 C4 -125.9(5) . .
C8 N1 C6 C5 52.5(7) . .
C8 N1 C7 O1 -179.6(5) . .
C8 N1 C7 C9 -0.5(5) . .
C8 C10 C12 C12 -6.6(8) . 6_554
C8 C10 C12 C14 179.9(4) . .
C9 C10 C12 C12 174.1(4) . 6_554
C9 C10 C12 C14 0.6(7) . .
C9 C11 C13 C14 -3.2(7) . .
C9 C11 C13 C15 -177.1(5) . .
C10 C9 C11 C13 4.2(7) . .
C10 C12 C14 C13 0.3(7) . .
C10 C12 C14 C16 -178.4(5) . .
C11 C9 C10 C8 177.5(4) . .
C11 C9 C10 C12 -3.1(8) . .
C11 C13 C14 C12 1.1(8) . .
C11 C13 C14 C16 180.0(5) . .
C11 C13 C15 O3 -3.1(9) . .
C11 C13 C15 N2 -179.8(5) . .
C12 C12 C14 C13 -173.5(5) 6_554 .
C12 C12 C14 C16 7.8(8) 6_554 .
C12 C14 C16 O4 1.4(9) . .
C12 C14 C16 N2 -178.7(5) . .
C13 C14 C16 O4 -177.5(6) . .
C13 C14 C16 N2 2.5(5) . .
C14 C13 C15 O3 -177.6(5) . .
C14 C13 C15 N2 5.7(5) . .
C15 N2 C16 O4 -178.8(5) . .
C15 N2 C16 C14 1.3(6) . .
C15 N2 C17 C18 -108.2(7) . .
C15 N2 C17 C19 75.7(7) . .
C15 C13 C14 C12 176.0(5) . .
C15 C13 C14 C16 -5.1(5) . .
C16 N2 C15 O3 179.0(5) . .
C16 N2 C15 C13 -4.2(6) . .
C16 N2 C17 C18 76.7(7) . .
C16 N2 C17 C19 -99.5(7) . .
C17 N2 C15 O3 3.4(9) . .
C17 N2 C15 C13 -179.8(5) . .
C17 N2 C16 O4 -3.1(9) . .
C17 N2 C16 C14 177.0(5) . .
C17 C18 C20 C22 -0.5(9) . .
C17 C19 C21 C22 -1.8(10) . .
C18 C17 C19 C21 -0.5(9) . .
C18 C20 C22 C21 -1.8(10) . .
C19 C17 C18 C20 1.7(9) . .
C19 C21 C22 C20 3.0(10) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125824
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
1 0.000 -0.956 0.000 523.5 10.2
2 0.088 0.250 0.250 523.5 10.2
3 -0.096 -0.250 0.750 523.5 10.2
4 0.500 -0.984 0.500 523.5 10.2
